{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T17:21:58Z","timestamp":1760548918324,"version":"3.40.5"},"reference-count":50,"publisher":"American Chemical Society (ACS)","issue":"7","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Org. Lett."],"published-print":{"date-parts":[[2010,4,2]]},"DOI":"10.1021\/ol902767b","type":"journal-article","created":{"date-parts":[[2010,3,1]],"date-time":"2010-03-01T14:10:52Z","timestamp":1267452652000},"page":"1396-1399","source":"Crossref","is-referenced-by-count":21,"title":["Highly Diastereoselective Synthesis of Substituted Pyrrolidines Using a Sequence of Azomethine Ylide Cycloaddition and Nucleophilic Cyclization"],"prefix":"10.1021","volume":"12","author":[{"given":"Guillaume","family":"B\u00e9langer","sequence":"first","affiliation":[{"name":"D\u00e9partement de Chimie, Universit\u00e9 de Sherbrooke, 2500 Boulevard Universit\u00e9, Sherbrooke, Qu\u00e9bec J1K 2R1, Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"V\u00e9ronique","family":"Darsigny","sequence":"additional","affiliation":[{"name":"D\u00e9partement de Chimie, Universit\u00e9 de Sherbrooke, 2500 Boulevard Universit\u00e9, Sherbrooke, Qu\u00e9bec J1K 2R1, Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Micha\u00ebl","family":"Dor\u00e9","sequence":"additional","affiliation":[{"name":"D\u00e9partement de Chimie, Universit\u00e9 de Sherbrooke, 2500 Boulevard Universit\u00e9, Sherbrooke, Qu\u00e9bec J1K 2R1, Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Fran\u00e7ois","family":"L\u00e9vesque","sequence":"additional","affiliation":[{"name":"D\u00e9partement de Chimie, Universit\u00e9 de Sherbrooke, 2500 Boulevard Universit\u00e9, Sherbrooke, Qu\u00e9bec J1K 2R1, Canada"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"316","published-online":{"date-parts":[[2010,3,1]]},"reference":[{"key":"ref1\/cit1","unstructured":"For a selection of reviews on the methods for the preparation of azomethine ylides and their 1,3-dipolar cycloadditions, see:"},{"key":"ref1\/cit1a","doi-asserted-by":"crossref","first-page":"2765","DOI":"10.1021\/cr040004c","volume":"105","author":"Coldham I.","year":"2005","journal-title":"Chem. Rev."},{"key":"ref1\/cit1b","doi-asserted-by":"crossref","unstructured":"bHarwood, L. M.; Vickers, R. J.InSynthetic Applications of 1.3-Dipolar Cyaloaddition Chemistry Toward Heterocycles and Natural Products;Padwa, A.; Pearson, W. H., Eds.Wiley:New York, 2003; pp169\u2212252.","DOI":"10.1002\/0471221902.ch3"},{"key":"ref1\/cit1c","doi-asserted-by":"crossref","first-page":"941","DOI":"10.1021\/cr00075a014","volume":"86","author":"Vedejs E.","year":"1986","journal-title":"Chem. Rev."},{"key":"ref2\/cit2","unstructured":"For the gerenation of unstabilized azomethine ylides from demetalation of (trimethylsilyl)methyl- or (tributylstannyl)methyliminium ions, see ref1and:"},{"key":"ref2\/cit2a","doi-asserted-by":"crossref","first-page":"6452","DOI":"10.1021\/ja00515a061","volume":"101","author":"Vedejs E.","year":"1979","journal-title":"J. Am. Chem. Soc."},{"key":"ref2\/cit2b","doi-asserted-by":"crossref","first-page":"1213","DOI":"10.1246\/cl.1981.1213","author":"Achiwa K.","year":"1981","journal-title":"Chem. Lett."},{"key":"ref2\/cit2c","doi-asserted-by":"crossref","first-page":"3939","DOI":"10.1248\/cpb.31.3939","volume":"31","author":"Achiwa K.","year":"1983","journal-title":"Chem. Pharm. Bull."},{"key":"ref2\/cit2d","doi-asserted-by":"crossref","first-page":"3447","DOI":"10.1016\/S0040-4039(00)86009-8","volume":"24","author":"Padwa A.","year":"1983","journal-title":"Tetrahedron Lett."},{"key":"ref2\/cit2e","doi-asserted-by":"crossref","first-page":"4006","DOI":"10.1021\/jo00221a010","volume":"50","author":"Padwa A.","year":"1985","journal-title":"J. Org. Chem."},{"key":"ref2\/cit2f","doi-asserted-by":"crossref","first-page":"5441","DOI":"10.1016\/S0040-4039(97)01217-3","volume":"38","author":"Pearson W. H.","year":"1997","journal-title":"Tetrahedron Lett."},{"key":"ref2\/cit2g","doi-asserted-by":"crossref","first-page":"1919","DOI":"10.1021\/jo030334h","volume":"69","author":"Pearson W. H.","year":"2004","journal-title":"J. Org. Chem."},{"key":"ref3\/cit3","unstructured":"For a selection of recent examples, see:"},{"key":"ref3\/cit3a","doi-asserted-by":"crossref","first-page":"2547","DOI":"10.1021\/ol900806m","volume":"11","author":"Pandey G.","year":"2009","journal-title":"Org. Lett."},{"key":"ref3\/cit3b","doi-asserted-by":"crossref","first-page":"1515","DOI":"10.1021\/ol9001653","volume":"11","author":"Burrell A. J. M.","year":"2009","journal-title":"Org. Lett."},{"key":"ref3\/cit3c","doi-asserted-by":"crossref","first-page":"2290","DOI":"10.1021\/jo8019913","volume":"74","author":"Burrell A. J. M.","year":"2009","journal-title":"J. Org. Chem."},{"key":"ref3\/cit3d","doi-asserted-by":"crossref","first-page":"3629","DOI":"10.1016\/j.tet.2008.02.008","volume":"64","author":"Carra R. J.","year":"2008","journal-title":"Tetrahedron"},{"key":"ref3\/cit3e","doi-asserted-by":"crossref","first-page":"6159","DOI":"10.1002\/anie.200701943","volume":"46","author":"Coldham I.","year":"2007","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref3\/cit3f","doi-asserted-by":"crossref","first-page":"4135","DOI":"10.1021\/jo0703799","volume":"72","author":"Pearson W. H.","year":"2007","journal-title":"J. Org. Chem."},{"key":"ref3\/cit3g","doi-asserted-by":"crossref","first-page":"1778","DOI":"10.1002\/1521-3773(20020517)41:10<1778::AID-ANIE1778>3.0.CO;2-R","volume":"41","author":"Epperson M. T.","year":"2002","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref4\/cit4","unstructured":"For example, see ref2f,2gand:"},{"key":"ref4\/cit4a","doi-asserted-by":"crossref","first-page":"5408","DOI":"10.1016\/j.tetlet.2008.07.010","volume":"49","author":"Coldham I.","year":"2008","journal-title":"Tetrahedron Lett."},{"key":"ref4\/cit4b","doi-asserted-by":"crossref","first-page":"12671","DOI":"10.1016\/S0040-4020(97)00788-6","volume":"53","author":"Alker D.","year":"1997","journal-title":"Tetrahedron"},{"key":"ref4\/cit4c","doi-asserted-by":"crossref","first-page":"5161","DOI":"10.1016\/S0040-4020(01)87128-3","volume":"47","author":"Roussi G.","year":"1991","journal-title":"Tetrahedron"},{"key":"ref4\/cit4d","doi-asserted-by":"crossref","first-page":"198","DOI":"10.1039\/p19890000198","author":"Grigg R.","year":"1989","journal-title":"J. Chem. Soc., Perkin Trans. 1"},{"key":"ref4\/cit4e","doi-asserted-by":"crossref","first-page":"47","DOI":"10.1039\/c39870000047","author":"Grigg R.","year":"1987","journal-title":"J. Chem. Soc., Chem. Commun."},{"key":"ref5\/cit5","doi-asserted-by":"crossref","first-page":"4939","DOI":"10.1021\/ol802010n","volume":"10","author":"L\u00e9vesque F.","year":"2008","journal-title":"Org. Lett."},{"key":"ref6\/cit6","unstructured":"Gin et al. recently reported a somewhat related method, although their system does not allow for an additional nucleophilic cyclization. See ref3d,3g."},{"key":"ref7\/cit7","unstructured":"Pearsonet al.already proposed a fast destannylation ofN-(tributylstannyl)methyliminium ions. See ref2g."},{"key":"ref8\/cit8","unstructured":"For the preparation of azomethine ylides bearing a carbon of a higher oxidation state, see also:"},{"key":"ref8\/cit8a","doi-asserted-by":"crossref","first-page":"5813","DOI":"10.1016\/S0040-4039(00)93562-7","volume":"32","author":"Ohno M.","year":"1991","journal-title":"Tetrahedron Lett."},{"key":"ref8\/cit8b","doi-asserted-by":"crossref","first-page":"12969","DOI":"10.1016\/S0040-4020(99)00805-4","volume":"55","author":"Washizuka K.","year":"1999","journal-title":"Tetrahedron"},{"key":"ref8\/cit8c","doi-asserted-by":"crossref","first-page":"4303","DOI":"10.1016\/S0040-4039(00)88326-4","volume":"24","author":"Padwa A.","year":"1983","journal-title":"Tetrahedron Lett."},{"key":"ref8\/cit8d","doi-asserted-by":"crossref","first-page":"3915","DOI":"10.1016\/0040-4039(96)00688-0","volume":"37","author":"Fishwick C. W. G.","year":"1996","journal-title":"Tetrahedron Lett."},{"key":"ref8\/cit8e","doi-asserted-by":"crossref","first-page":"945","DOI":"10.1246\/cl.1997.945","author":"Tsuge O.","year":"1997","journal-title":"Chem. Lett."},{"key":"ref9\/cit9","unstructured":"Synthesis described in theSupporting Information."},{"key":"ref10\/cit10","unstructured":"Activation with triflic anhydride was problematic due to competitive irreversible activation ofN-phenylmaleimide."},{"key":"ref11\/cit11","unstructured":"Less polar solvent, such as toluene, caused the precipitation of polar intermediate(s), and the yield was dramatically affected."},{"key":"ref12\/cit12","unstructured":"2,6-Di-tert-butyl-4-methylpyridine could be employed as well, resulting in similar yields. The use of other bases, or no base at all, resulted in a significant decrease in the overall yield."},{"key":"ref13\/cit13","unstructured":"Azomethine ylide intermediates should be trapped as soon as they are formed in the reaction medium. The use of 3 equiv of dipolarophile was optimal; below this level, extensive decomposition and low yields were obtained."},{"key":"ref14\/cit14","unstructured":"See theSupporting Information."},{"key":"ref15\/cit15","unstructured":"Pyrroline14was isolated because of the lower nucleophilicity of the vinylogous carbamate moiety of14(compared to a vinylogous urea moiety whenN-phenylmaleimide is used) that hampered its in situ activation."},{"key":"ref16\/cit16a","doi-asserted-by":"crossref","first-page":"4431","DOI":"10.1021\/ol0516519","volume":"7","author":"B\u00e9langer G.","year":"2005","journal-title":"Org. Lett."},{"key":"ref16\/cit16b","doi-asserted-by":"crossref","first-page":"704","DOI":"10.1021\/jo052141v","volume":"71","author":"B\u00e9langer G.","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref17\/cit17","unstructured":"Chloride anion (n-Bu4NCl) promoted the destannylation as well, albeit in lower yield."},{"key":"ref18\/cit18","doi-asserted-by":"crossref","first-page":"711","DOI":"10.1007\/s00204-005-0002-z","volume":"79","author":"Thomas L. D.","year":"2005","journal-title":"Arch. Toxicol."},{"key":"ref19\/cit19","unstructured":"Formation of 5-membered rings by via Vilsmeier\u2212Haack cyclizations gives poor yields, as previously demonstrated (see ref16)."},{"key":"ref20\/cit20","unstructured":"Relative stereochemistry on19was proven by comparison with the X-ray diffraction stucture of the analogousp-bromo-substituted phenyl derivative (see theSupporting Information)."},{"key":"ref21\/cit21","unstructured":"The enol ether was not compatible with POCl3activation, resulting in partial hydrolysis."},{"key":"ref22\/cit22","doi-asserted-by":"crossref","first-page":"66","DOI":"10.1021\/ar020094c","volume":"36","author":"Mayr H.","year":"2003","journal-title":"Acc. Chem. Res."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ol902767b","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,3,15]],"date-time":"2023-03-15T17:18:45Z","timestamp":1678900725000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ol902767b"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2010,3,1]]},"references-count":50,"journal-issue":{"issue":"7","published-print":{"date-parts":[[2010,4,2]]}},"alternative-id":["10.1021\/ol902767b"],"URL":"https:\/\/doi.org\/10.1021\/ol902767b","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"type":"print","value":"1523-7060"},{"type":"electronic","value":"1523-7052"}],"subject":[],"published":{"date-parts":[[2010,3,1]]}}}